And stanley krall



F fncture,

Reissued June 7, 1927.

NORMAN A. SHEPARD, OI AKRON, OHIO, MASSACHUSETTS, ASSIGNOBB TO THE Original 10. 1,516,072, dated No, muse This invention relates to the process of vulcanizing rubber and particularly to a new and improved method of combining rubber with vulcanizing agents to produce 5 improved results in operation.

It relates specifically to a new and useful method of accelerating ,the vulcanization of rubber by the addition of certain organic substances, as accelerators which are in- 10 tended to'quicken the process of vulcanization and to im rove the qualitiesof the cured or vulcanized rubber.

known and studied for many years, but all 15 of said substances are not suitable for use in obtaining stocks possessing certain characteristics and others, while possessing marked acceleratin properties, have had a limited commerciaf application owing to difiiculties attendant upon their use. Certain of said accelerators are-too volatile and loss occurs in the milling and calendaring. The fumes given ofi are objectionable and sometimes toxic so as to be dangerous to 25 use and requiring special ventilating equipment. Other disa vantages are present in certain known accelerators which render them unsuitable for various reasons. I It is the purpose of the present invention to make use of certain substanceswhich have heretofore been unused in the vulcanization of rubber, which substances do not have anyof the disadvantages which have been described,

can be worked into rubber compounds without disagreeable results and which will mix well in the compounds with out loss due to the excessive volatilit The substances which have been eveloped by us are formed by the condensation of aldehyde-ammonias with mustard oils or thiourea, which are then incorporated in the rubber mix in the usual manner.

The reaction product of amataldehvdeammonia with phenyl mustard oil has been PfiOCESB OF VULCANIZIHG RUBBER AND COMPOUH Rubber accelerators, so called, have been are easy and cheap to menu-- a Re, 15,648

-UNITED STATES PATENT OFFICE.

AND STANLEY KRALL, 0F LONGMEADQW, FIRESTQHE TIRE AND RUBBEB COMIANY,

O1? AKRON, OHIO, A CORPORATION OF OHIO.

n RESULTING 'rrmnnrmm,

No Drawing. .Orlginal application filed June 20, 1923, Serial No. 846,702, Renewed August 4, i925, larch 9, 1928. Application for reissue filed January 15, 192?, serial ascribed the following formula by Dixon This compound is l-phenyl-Q-thiocarbonyl- 4, 6-dimethyl--hexahy( ro-l, 3,

from objectionable odor, and for use as an accelerator of of rubber,

fi-triazine. It

- is non-volatile, well crystallized and is free is well suited vulcanization Similar products'may be obtained by the reaction of other mustard oils (isothiocyanates) Th us upon other aldehyde-ammonia. from allyl mustard oil and acetaldehyde-ammonia is obtained 1-allyl-2-thiocar bonylA, B-dimethyl-hexahydro-l, 3, b-triazine; while from bu raldehyde is car onyl-4,

henyl mustard oil and I o tained I-phenyI-Q'thim -6-di-butyl-hexahydro-1, U 5- triazine; and all of these reaction products are within the broad scope of the present.

invention, being rapid, easily handled and superior accelerators.

An example of the activity erators of vulcanization is as follows:

l-93.5 parts of these accelparts of zinc oxide and 1 part of 1-phenyl-2-thiocarbonyl-4, fi-dimethyl-hexahydrml, 3, IS-trinzine and heated in a vulcanizer for fortyfive minutes at 290 F. The

roduct is well cured and vulcanization so taken place in one-fifth of the time of heating required to produce similar physical prop 'erties without the addition of the accelerator.

It will be appreciated that the formula;

given above are not restrictive oi the invention and that as far as known to us we are the first to make use 0 f the 7 reaction I ll of smoked sheet are mixed products of aldehyde-aminonias with mustard oils or thiourea for acceleration of rubber vulcanization.

\Vhat We claim is:

1. The process of vulcanizing rubber which Comprises incorporating with rubber -a small amount of av reaction product of an aldehyde-ammonia with a mustard oil,

and heating the resultant product with a vulcanizing agent, I

The process of producing vulcanized rubber which comprises incorporating with the a or 6-difi-triazine and heatproduct with a vulcanizing derivative of Z-thiocarhonyl-l metl1yl-llexuhydro-l, 3, ing the resulting agent. a

3. The process. of producing vulcanized rubber which comprises incorporating with rubber a small amount ofa homologue the rubber a small amount of l-phenyl-2- thiocarbonyl, fi-dimethyl-hexahydro-1, 3, S-triazine, and heating the resulting product with a vulcanizing agent.

4. A. vulcanized rubber having incorporated therein a small amount of the reaction product of an aldehyde-ainmonia with a mustard oil.

5. A vulcanized rubber having incorpo rated therein a small amount of a homologue or derivative of Q-thiocarbouyld, 6- dimerhyl-hexahydro-l, 3, fi-triazine.

6. A vulcanized rubber having inc0rp0- rated therein a small amount of l-phenyh 3thimaarlroxjryl-i, (i-diniet'hyl-l1e ;ah ydr01,3, Z-triazine.

NORMAN A. SHEPARD. STANLEY KRALL. 

